Tetraacetylethane

Tetraacetylethane is the organic compound with the nominal formula [CH(C(O)CH₃)₂]₂. It is a white solid that has attracted interest as a precursor to heterocycles and metal complexes. It is prepared by oxidation of sodium acetylacetonate:^[1]

I₂ + 2 NaCH(C(O)CH₃)₂ → [CH(C(O)CH₃)₂]₂ + 2 NaI

Tetraacetylethane

Names
Other names 3,4-diacetyl-2,5-Hexanedione
Identifiers
CAS Number	5027-32-7 Y
3D model (JSmol)	Interactive image
ChemSpider	71074
EC Number	225-718-3
PubChem CID	78730
UNII	FJ6RVQ86SM
CompTox Dashboard (EPA)	DTXSID60198270
InChI InChI=1S/C10H14O4/c1-5(11)9(6(2)12)10(7(3)13)8(4)14/h9-10H,1-4H3 Key: CSKRBHOAJUMOKJ-UHFFFAOYSA-N
SMILES CC(=O)C(C(C(=O)C)C(=O)C)C(=O)C
Properties
Chemical formula	C10H14O4
Molar mass	198.218 g·mol−1
Appearance	white solid
Density	1.305 g/cm3
Melting point	192–193 °C (378–379 °F; 465–466 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Reminiscent of the case of acetylacetone, tetraacetylethane exists as the enol, as established by X-ray crystallography. The two C₃O₂H rings are twisted with a dihedral angle near 90°.^[2]

Many metal complexes have been prepared from the conjugate base of this ligand. One example is diruthenium(III) derivative [Ru(acac)₂]₂[C(C(O)CH₃)₂]₂, which is closely related to ruthenium(III) acetylacetonate.^[3]